


Room Over the Garden

by RedString_OfFate



Category: Critical Role (Web Series)
Genre: Barebacking, Consensual, F/M, Friends With Benefits, Loss of Virginity, One Shot, Orgasm, Plot What Plot/Porn Without Plot, Quiet Sex, Scars, Tenderness, Vaginal Fingering, Virginity
Language: English
Status: Completed
Published: 2020-02-13
Updated: 2020-02-13
Packaged: 2021-02-28 07:13:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,805
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22689799
Author URL: https://archiveofourown.org/users/RedString_OfFate/pseuds/RedString_OfFate
Summary: Caleb and Jester love each other. They're just not IN love. But they trust one another, and have their own reasons for their tryst.
Relationships: Jester Lavorre/Caleb Widogast
Kudos: 94





	Room Over the Garden

**Author's Note:**

> Feel free to leave your thoughts, and requests below. This is just a scene I've been mulling over the last couple days. I've not written in a VERY LONG time, so I am a bit rusty.

“Cayleb?” 

It was the middle of a shopping day, when all of the Mighty Nein were out and doing their own thing. Naturally, Caleb stayed at the inn to get some studying in. Jester went out only for fresh air, and to get a few muffins, and returned to catch him on his own.

She put a bag down in front of him. 

“I got you a pastry.”

Blue eyes looked up at her, and she beamed. 

“Ah.. Jester. I thought you went out with the others? Is something the matter?” The wizard closed his book and straightened his back a little. 

The Little Sapphire took in the sight of her friend. He was handsome for a man who only just learned to clean himself. There was something very charming about the way he tied his hair back when he read, and rolled up the sleeves of his shirt. Especially now that he’d stopped hiding so much. He always looked deeply worried about something though. Or mournful. Or both. 

“Okokok..” Jester sat down nervously. She slid her hands over her skirt, noticing her palms were a little clammy. “Actually… I wanted to get a moment to talk to you alone. Also, the muffin!” She made a point to puh the bag closer. “It’s cranberry!”

The man looked at the bag, then back to his friend. “ _Ja._ Jester. That is thoughtful.” He narrowed his eyes. “You seem nervous. So I ask again. Is something the matter, my friend?”

Ah. She could feel the sweat gathering under the layers of her pretty dress, and all her muscles bunching up. She just needed to get it over with. Ask. If he said no, they could just move on. 

Leaning in very close, she beckoned Caleb with her hand to come closer across the table as well. He obliged, leaning in so close she could smell him. Bliblichor. 

“Caleb,” she whispered. “I want you to have sex with me.”

Red-faced, Caleb averted his gaze and covered his mouth. Leaning back in his chair, it was clear how shocked he was. How he’d never imagined this to be what she’d wanted from him. 

“I’m not in love with you!” Arms outstretched, Jester reacted just a little too loudly and drew the gaze from some other patrons. She uttered a flustered apology to the room, and leaned back over the table. 

“I’m not in love with you. I just… I really trust you and I think you will be kind to me and I don’t want to be bad at sex, you know? And you are a guy who knows a lot about things, and I know you read a lot of porn-”

If it was possible for Caleb to get more red, he would have. Listening to her ramble, he just sat there like a stone. 

“-And I think that maybe it would be good for you to get to touch someone again because ever since I’ve known you I have never seen you go off with anyone, and I think I could also be kind to you, you know?” 

Her purple was as brilliant as his red. She brought her hands up to cover her own mouth, not knowing she was, in a way, mirroring his body language. Both of them forgot to breathe for a moment. 

“... _Ja._ ” He looked down. “Ok. Let’s… Do that.”

It was Jester’s turn to be shocked. 

“Wait. Really?!” Too loud, once more she had to apologize to those around them who no doubt started listening in. The little blue tiefling got up and rushed around the table. She stood there, and then hugged Caleb aggressively. He just sat there in her arms, with a slightly embarrassed smile on his face. 

“Thank you, Caleb.” She gave him a peck on the cheek and rushed towards the stairs. Before she got all the way up the flight though, she ran back over to the table. “Oh I forgot we need to, like, you know. Choose a time. How about… In like an hour? Everyone else is probably going to be out for a while still, so our rooms are free!”

He nodded.

“Okokok.” She went to rush off again, but had to turn around. This time she just called from the steps. “Don’t forget to bathe!”

She winked, and went to prepare.

\--

Books had taught Jester many things, and preparing for a night of romance was on that list. Though romance was not actually what she had in mind, she still wanted it to be nice. So she brushed her hair, put on some rouge, and used a spell to make her room smell like vanilla.

In nothing but a sleeveless linen slip, Jester gave a twirl in the middle of her room. She felt good. Excited. 

Padding over to the double doors that lead to the balcony, Jester wanted to bring in some fresh air as the vanilla was tinged with dust. It was a rather nice inn, but there was still a stuffiness to it. She opened the room up, took in a deep breath, and looked out over the garden. It was crisp, and not much was in bloom, but it was still beautiful. In just a few months, she would imagine how colourful and bright it would be. But for now, she could settle for the nature of it all, and the view of a sky that was slowly turning orange.

It was quiet, save for a bird singing in one of the small trees.

So lost in thought, Jester hadn’t noticed when Caleb entered the room. He was just at the balcony before she turned to see him. Instantly she smiled. 

Ginger hair damp, and loose around his face, Caleb looked like he’d really put an effort in to clean up for her. He only wore his trousers, and his undershirt with the sleeves rolled up, but everything was clean. It was sweet. He looked out past her, then directly into her eyes. 

“Are you absolutely sure, Jester?”

She nodded. 

“ _Ja._ Ok. Turn around.” 

With only a second of hesitation, Jester did as she was asked. She turned, and rested her elbows back on the wooden railing she had been propped up just moments before. Not that she had noticed, but there was a smile on her lips the whole time. 

Hands reached around her waist, and Jester felt her friend press himself into her back, curling around her smaller frame. He held her in a tight embrace, and buried his head into the back of her neck. There they stood, overlooking a quiet garden, for a long minute. Jester felt warm. Not just from Caleb’s warmth, but from anticipation. She looked down to see her nipples hard against the white of her slip, and Caleb's hand slowly moving up to grasp her ample chest. 

Everything he did was slow, but firm. It was like he was planning everything out with the idea in mind to perfectly execute each movement. 

As he squeezed her breast, Jester could feel him stiffen against her back. She couldn’t help herself, and automatically arched her back to press her backside into him. 

Hot breath against her ear, Jester closed her eyes. It tickled, and she let out a quiet giggle. 

“If at any point you do not like this, or are uncomfortable, just say so, ok?” He squeezed her around the middle more tightly as his finger pinched her nipple through the linen. 

She nodded, and the arm around her waist slid down her side and the other hand found her thigh.

“What do you want me to do, Jester?”

His fingers worked the hem of her slip up so he could drag his nails along her thigh. Not roughly, but enough. 

Jester was lost for words. She’d felt excited before sexually from her books, and even her own thoughts. But this, being touched in this way, was something more. It took him prompting her once more with a whisper in the ear for her to respond. She only turned her face to look at him. 

“I want you,” she uttered almost inaudibly, “to take me right here, Caleb.” Her voice wasn’t steady, but neither of them brought attention to it. 

Jester let her left arm glide along her partner’s. She could feel his scars as she went to find his hand. Jester gripped his hand to make it so his nails dug into her thigh more firmly. Her right hand went to the one he had on her chest. She guided him into the side of the slip so he could hold her bare breast. 

The older man made sure to press his whole body into hers so she was firmly trapped against the railing. Nails biting into her skin at her own urging, Jester let her head roll back against Caleb’s shoulder, eyes closed, careful not to catch him with her horn. He kissed her neck hungrily. It was this that brought a small moan to the back of Jester’s throat. 

“Cayleb…” She was trying to be quiet so as not to bring attention to them from anyone who could possibly step out onto their own balcony and catch them. 

His hands were rougher than Jester had expected. They were stronger too. Masculine. Those hands were now roaming on their own as Jester reached up to hold his damp hair back with a firm tug. She pressed her bottom into him again, not only to give him a good feel of her ass, but to create more room for his hands on her thighs. Both were there now as he found her. She was already wet.

Jester let her tail flick between his legs, letting the base of it play at his groin. It was Caleb’s turn to let a low rumble from his throat, which he made sure she heard by biting her ear. 

A tingle ran up her spine from the bite and the finger that pressed at her entrance. Caleb started slowly pressing his pointer finger inside of her. She was tight, but ready for him. He made sure she had time to adjust before adding a second finger and pulling them almost all the way out before going back in. And out, and in. She was squirming in his hands the moment his thumb found her clit, stimulating it with small circles as he played with her. 

At this point Jester could feel another moan coming. She tightened her grip on his hair, and turned her face to his. She kissed him then, letting her right hand find the balcony again to steady herself. 

Caleb flicked his tongue along her bottom lip, inviting her to a deeper kiss as he fingered her. Both of them keeping as quiet as they could. 

“I want you inside of me, Caleb.” She whined into his mouth, and pulled away only enough to look into his warm eyes. 

“ _Ja,_ ok.” he pulled his fingers out of her slowly, laboriously bringing his fingers to his own mouth, making a show of it. He was making sure she could see him taste her. It seemed out of character, but then again, maybe this was how he’d always been behind closed doors. It turned her on more.

Twisting in the small bit of space she had, Jester clawed at the tie in the front of Caleb’s pants. It was the first time she’d gotten to see the length of him, pressed painfully against the rough spun fabric. A moment of worry flashed across her face. It’s not that it was huge, but the idea of all of him fitting inside of her made her hesitate. 

“Jester? You are still ok?” He reached to hold her face, to find her gaze in his own. 

“Yes.. Yes. Please.” She went back to releasing him, and was careful not to get him with her long nails. She read that that could hurt men, and so was mindful of his sensitive skin 

He was pale, which should not have surprised her. They’d all bathed together before, but she never looked at him in this way. With his penis engorged and already slick with the thought of her. 

“Rest your elbows on the railing,” he brought her back into the moment. He deftly untied the front of her slip halfway, so he could see more of her beautiful blue chest. With her boobs spilling out the pale linen, purple nipples firm, Caleb gave himself a few pumps.

“Cayleb, you’re teasing me,” she hissed. Not angry, but hungry. 

To this, he actually smiled. Something warm, and comfortable as he looked at her. 

“ _Bitte_?” He shook his head, and reached out for her hands. Guiding her once more, he brought her hands around the back of his head. “Hold on, _mein Saphir._ ” It was then he grabbed her thighs, and lifted her. 

Again, surprise. Jester let out a little shocked sound before laughing, and looking at Caleb. If he was struggling to lift her, he wasn’t showing it. It was actually impressive how he was able to-

He pressed into her slit, missing only once and rubbing against her. He was slow, methodical, and concentrated. Jester gasped. It hurt to have him enter her, but he was doing his best to make it gentle. Her grip around his neck tightened a little as she pressed her forehead to his, slamming her eyes shut. 

“Mm.. Cayleb, keep going,” she urged him on. There was pain, but wrapped in pleasure.

If Jester had thought she was warm before, then she was on fire now. The air was cool, but the sun was adding to the moment with its orange light, giving the wizard a glow that made Jester hunger for him even more. Bucking her hips, she forced him into her completely, and it took everything in her not to scream out. She bit her own lip hard, and she was sure it would be fat later. 

It took a few seconds for him to start moving again, but Caleb found a middle ground between perching his lover on the railing, and holding her weight on his own. Pressing her into the wood, he made sure to check to make sure she was ok. She just urged him on, nodding furiously. 

He started finding his rhythm with her there. Jester’s comfort with him inside of her became even more clear when she let her head fall back and she started fondling her own nipple. She was still careful to hold on to him, as he was to her, but they found pace together. The tiefling even discovered she could feel him in her more if she bounced in time with his thrusts. 

Together, they worked faster, and save for their ragged breaths, and the sound of skin-on-skin, they were silent. Harder, and more vigorously, Jester allowed herself to just enjoy the freeing feeling of being half nude under the sky, with her friend fucking her in silence. She could feel a coil inside her stomach before she looked back to Caleb.

The human was drinking in the sight of the woman on his cock, thrusting furiously into her. She bunched up her slip so she could watch him go in to her. 

“I thi- I think I am going to-”

She came, fist going to her mouth, letting go of her clothing. She bit down on her finger to keep from screaming.

Jester could hardly feel her body as she twitched on the length of her companion, thighs clenching around his body. He said something, but she was in no way to hear words. She felt herself fill with a warmth she didn’t expect and her eyes rolled closed. 

It took a minute before she realized they were just there, clinging to one another. Caleb was sinking as slowly as he could to his knees, careful not to drop the precious cargo in his arms. 

Once safe on solid ground, Caleb laid Jester down on the balcony, and pulled himself from her body. He kissed her softly on the lips, then the jaw, the neck, the collarbone. He let his body lay on top of hers, face resting on her chest.

Jester let her fingers find his curled hair which was now damp from more than just his earlier bath. She held him there as long as she could stand the cold. 

With their session over, and the sky turning dark, the temperature had dropped significantly. So, together they cleaned up best they could, and went back inside.

Before parting ways, Jester leaned on her door frame. She was still positive she was not in love with Caleb, but it was clear there was a bond here that was deeper thanks to their evening together. She patted his chest. 

“Thank you, Firebringer.”

“Goodnight, Jester.”


End file.
